Each year when I start seeing winter squash all over the produce section of all my favorite grocery stores, I go a little “squash-happy” – wanting to roast squash for just about every meal.

I’m not kidding! Butternut, acorn, pumpkin, delicata. It’s all waiting for me to roast and figure out new, fun ways to EAT it!

Luckily, I’m not usually at a loss when it comes to squash. Whether I’m stuffing a turkey with it, stuffing the squash itself or using it in a pie, I thoroughly enjoy my winter squash cooking adventures.

However, today, as you might have already noticed, we’re not stuffing anything! We’re going light and sweet with a roasted butternut squash salad!

Each year I love making a variation of this salad with fresh crispy apples (pink ladies are my favorite), toasted pecans, raisins or dried cranberries and fresh greens.

The ultimate topper? A creamy, slightly sweet but tart buttermilk dressing. Trust me – the combination is just so tasty. I have to say that this dressing is downright addicting!

Now, I had my heart set on creating a Whole30 version of a maple-sweetened dressing I made in the past, so I turned to my favorite Medjool dates to help sweeten the dressing a notch.

It’s by no means an overly sweet dressing though. Rather, the sweet part is balanced by both savory and tart flavors that blend together to create a totally healthy, dairy-free, paleo, vegan and Whole30 buttermilk dressing!

We have coconut milk to thank for the creamy texture, which blends up so well with the dates to create a great base.

Combined with the creamy base and a bit of brown mustard, spices and sea salt, this salad dressing is one you’ll want to use on everything! It’s also a fun change from the usual vinaigrettes.

As for the rest of the salad, as usual, it’s all about my favorites! I make sure I roast my butternut squash perfectly, so it caramelizes just right to maximize the incredible natural sweetness in the squash.

A little bit of sea salt and cinnamon make it so tasty that it’s hard to not eat all of it right out of the oven. Seriously, this is a struggle – you’ve been warned!

Let’s get our butternut squash cubed and ready to roast! And the dressing made – it’s just sooo good. I’m excited for you to try this one – hope you enjoy!

Instructions

Dressing:

In a food processor or high powered blender, blend the dates, coconut milk and Organic Apple Cider Vinegar until smooth (a few date pieces are fine) Add in the mustard, salt, cinnamon, onion and garlic powder and blend until smooth. Transfer to a container, cover and refrigerate until ready to use.**

Salad:

Preheat your oven to 425 degrees. Put the cubed butternut in a bowl with 1.5 Tbsp melted coconut oil and toss to coat. Sprinkle with about 1/2 tsp sea salt, then spread out in a single layer on a large baking sheet lined with parchment paper.

Roast for about 30-40 minutes total until golden brown and soft. Midway through, sprinkle with 1/2 tsp apple pie spice (or cinnamon) and stir or shake gently to evenly brown.

Meanwhile, toss chopped pecans with remaining coconut oil, sea salt, and apple pie spice or cinnamon, and spread out on a separate baking sheet. Roast in the oven with the butternut for 5-7 minutes, checking to avoid burning. Remove promptly and set aside.

To assemble salad, layer the greens in a large bowl or platter, followed by the roasted butternut and sliced apples, toasted pecans and raisins or cranberries. Serve the dressing on the side, or drizzle over the top before serving.

Serves 6-8 as a side salad, or add your favorite protein to make it a meal!

Recipe Notes

*Soften the dates by soaking in boiling water for a couple of minutes, then drain. You can also sweeten the dressing with 1 Tbsp pure maple syrup, although this makes the recipe no longer Whole30 compliant. **Leftover dressing should be stored covered in the refrigerator for up to 4 days.

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About Michele

More than a little into running and paleo recipes (yoga now too!) but I'm not here to rain on your grains (or anything else) so come along for the ride! I do a little too much of everything (except cleaning), and I enjoy laughing at myself. As long as I'm the one making the jokes, that is. Just kidding. So bring me your angst, your appetite and your frying pan and climb aboard!

Just made this for my family of 4 and it was a success! It was a great combination of flavors. The only thing I did differently was use almond milk instead of coconut milk and the dressing was very watery which was expected but the flavor was still awesome. Great recipe! Thank you!

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Welcome!

Hi! I’m so happy you stopped by! My name is Michele and I’m a Paleo eater and recipe creator, runner, mom of 3, and the gal behind Paleo Running Momma! Over here you’ll find real-food, clean eating family favorites that you’ll be excited to share with your loved ones. I hope you stay awhile, eat, savor, and enjoy!